One of the best cities in the world is Chicago, IL. Okay we might be a little biased as this is our hometown. But Chicago is great city to visit with lots to offer. We recently spent the weekend here and had a great time. Since we live in Florida now, it was fun getting to be tourists! Here is our itinerary for 3 days in Chicago. Obviously you could spend much more time here, but if all you have time for is a quick weekend getaway then this is a great way to see some of the highlights of the city.

The Bean: Weekend in Chicago

Day 1

We flew in really early on a Saturday into Midway Airport. Our flight actually landed at 8:30AM so we had pretty much the entire day to explore. We spent our first day in the Millennium Park area. It was such a gorgeous day we wandered around Millennium Park, Grant Park, and Museum Campus. Millennium Park is where you can take the famous selfie with The Bean. (The Bean’s official name is ‘Cloudgate’ but nobody actually calls it that.) We then walked down to Grant Park to see Buckingham Fountain. The lakefront looked so beautiful that we strolled along the path until we got down to the Museum Campus. This is where the Adler Planetarium, Shedd Aquarium, and Field Museum are located. Right next door is Soldier Field where the Chicago Bears play. We did so much the first day we were exhausted!

Navy Pier: Weekend in Chicago

Day 2

The next day was spent at Navy Pier. Even though we have been to Navy Pier many times, they recently redid some of it so it was like going to a whole new place. They also opened up the new Centennial Wheel this year after replacing the original one. There are lots of shops and restaurants with great views of the city. This is also where you can take sightseeing boat trips, lunch/dinner cruises, and lots more. One of our favorite areas is the Beer Garden, which is located towards the end of the pier. There is usually live music and it is a fun place to grab a drink, relax, and people watch.

Navy Pier is also home to the Chicago Shakespeare Theater, IMAX Theater, kid-friendly attractions like the Chicago Children’s Museum and Chicago Fun House Maze, Stained Glass Gallery, and lots more. If you finish up everything at the Pier, the Riverwalk is a quick stroll from the entrance.

(Keep your eye out for the mural ‘Pier People‘ done by one of our friend’s cousins, Pete Nawara!)

Wrigley Field: Weekend in Chicago

Day 3

Take me out to the ballgame…take me out to the crowd! Today was spent in Wrigleyville and at Wrigley Field for a Cubs game! Wrigley Field is one of the oldest baseball stadiums in America and the home of our favorite team, the Chicago Cubs. (Wrigley was built in 1914. The oldest ballpark is Fenway in Boston built in 1912). The area around the park is known as Wrigleyville. There are so many bars, restaurants, and souvenir shops. This is one of the hotspots in the city for nightlife.

Even if you do not like baseball, it is worth going to see the park and Wrigleyville. If you do not want to sit through a baseball game, you can take a tour of the park for about $25 a person. The easiest way to get to Wrigley Field is to take the CTA Red Line and get off at the Addison stop.

Lou Malnati's deep dish pizza...a must when visiting Chicago!
Lou Malnati’s deep dish pizza…yum!

Chicago Travel Tips

*We lucked out with great weather. However the weather can be unpredictable, so pack some layers just in case.

*Try to stay downtown. You can easily walk to so many places. If you cannot find a hotel downtown, make sure you stay near an ‘L’ station or Metra station. This way you can easily take public transportation around instead of renting a car. Parking is very expensive downtown.

*Famous Chicago foods: Chicago style hot dog, deep dish pizza from Lou Malnati’s, roast beef sandwich from Al’s, Garrett’s popcorn (None of this is remotely healthy but even we cannot pass up some Lou Malnati’s pizza.)

*Chicago in the summer is the best. There are so many festivals, street fairs, and special events going on outside. Many of these are free. We personally think that is the best time to visit the city. Check out the city’s website for what’s going on.

*Both O’Hare and Midway Airports are easily accessible by public transportation. O’Hare is closer to the North Side while Midway is on the South Side.

Have you ever been to Chicago? What are your favorite things about the city or is Chicago still on your list of cities to visit? Let us know in the comments!

The Traveling Gals

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Weekend Getaway: Chicago, IL

50 thoughts on “WEEKEND GETAWAY: Chicago, IL”

  1. I love Chicago! I spent a week there a few years ago and it was amazing…however it was winter and a lot colder than it looks in your pics! Definitely want to go back in summer sometime!

  2. Sounds like a great weekend! I was there for a weekend a few weeks ago and didn’t want to leave!! My favorite spot was the rooftop at the Chicago Athletic Club!

  3. Wonderful tips! I recently went to Chicago for the first time, and although it was a work trip I definitely enjoyed the trip. I wish I had time to do all the things on your list – but I’m happy to say I was able to try Lou Malnati’s. Deep dish is something else!!! Great post.

  4. Wow! Looks like y’all had fun! Those are great tips, definitely something I’ll come back to if we ever travel to Chicago. I want to go just for that pizza, OMG!

  5. Ah loveee this! I took a weekend trip to Chicago a couple months ago. I already want to go back! Loved it. That pizza, YUM! I just posted about a recent trip to Seattle actually. Love to travel. xx, E

    1. Absolutely! That is the one thing we did not have time for. Michigan Ave, State Street, and Water Tower Place are some of our fave places to shop! 🙂

  6. This seriously looks like such a great city. Chicago is high on our list after talking with several locals and learning that Chicago has so much to offer families. Now after looking at this I can see why you love your city. Can’t wait to book a trip there.

  7. I’m a Chicagoan, so I totally agree with your suggestions. Lou Malnati’s has the BEST deep dish in my opinion. Some other fun things to do is to take a double decker bus tour of the city, or go shopping on State Street and Michigan Avenue.

  8. I’ve always wanted to visit Chicago and take a picture with the Bean lol. Your pictures are great. I had a discussion the other day about which pizza is better…NY or Chicago? Any opinion on this? I’ve never had Chicago pizza but I find it hard to believe anything is better than NY pizza.

    1. Haha well this is an unpopular opinion, but I prefer NY pizza! Although if you do go to Chicago, I would recommend trying Lou Malnati’s deep dish pizza. It is very good.

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